Hydrophobic extenders in fluorinated surface effect coatings

Patent metadata

Field	Value
Publication number	US-11359099-B2
Application number	US-201615764933-A
Country	US
Kind code	B2
Filing date	Sep 30, 2016
Priority date	Oct 2, 2015
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

The present invention relates to a coated article comprising a partial or complete fluorinated coating on the surface of an article, wherein the coating comprises 5 to 99% by weight of a hydrophobic compound, and 1 to 95% by weight of a fluorinated surface effect agent, both based on the total solids weight of the coating, where the hydrophobic compound is selected from a hydrophobic cyclic or acyclic ester alcohol.

First claim

What is claimed is:

1. A coated article comprising a complete permanent fluorinated coating on the surface of an article,
wherein the coating comprises 5 to 99% by weight of a hydrophobic compound, and 1 to 95% by weight of at least one fluorinated surface effect agent, both based on the total solids weight of the coating, wherein the hydrophobic compound is of formula (Ia):

wherein each R is independently —H; —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ;
each n is independently 0 to 20;
each m is independently 0 to 20;
m+n is greater than 0;
r is 1 to 3;
a is 0 or 1;
p is independently 0 to 2;
provided that a is 0 when r is 3;
each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons;
each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons; and
at least one R is —H and at least two R groups are a —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ;
wherein the fluorinated surface effect agent is a hydrophobic polymer selected from the group consisting of fluorinated cationic acrylic polymers, fluorinated anionic acrylic polymers, fluorinated nonionic acrylic polymers, partially fluorinated urethanes, and mixtures thereof; and
wherein, if the fluorinated surface effect agent is a fluorinated acrylic copolymer, it is a reaction product of monomers comprising:
a) one or more fluorinated ethylenically unsaturated monomers;
b) an ethylenically unsaturated monomer having a polar or reactive group; and
c) one or more monomers selected from a second ethylenically unsaturated monomer having a polar or reactive group, or a non-fluorinated ethylenically unsaturated hydrophobic monomers excluding cyclohexyl acrylate or methyl acrylate wherein the homopolymer of hydrophobic monomer c) has a maximum glass transition temperature (T g ) of 45° C. and/or a maximum melt transition temperature (T m ) of 25° C.

2. The coated article of claim 1 , where the hydrophobic compound is selected from formula (Ia) to be formula (la′):

wherein R is further limited to independently —H; —R 1 ; or —C(O)R 1 .

3. The coated article of claim 1 , where the hydrophobic compound is selected from formula (Ia) to be formula (la′):

wherein R is further limited to independently —H; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .

4. The coated article of claim 1 , where the hydrophobic compound is substituted with at least three —R 1 , —C(O)R 1 ,
(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 , or mixtures thereof.

5. The coated article of claim 1 , wherein the surface effect is no iron, easy to iron, shrinkage control, wrinkle free, permanent press, moisture control, softness, strength, anti-slip, anti-static, anti-snag, anti-pill, stain repellency, stain release, soil repellency, soil release, water repellency, oil repellency, odor control, antimicrobial, sun protection, anti-blocking, cleanability, dust resistance, leveling, corrosion resistance, acid resistance, anti-fog, anti-ice, or tanning.

6. The coated article of claim 1 , where the coating comprises 10 to 90% by weight of the hydrophobic compound, and 10 to 90% by weight of the fluorinated surface effect agent, both based on the total solids weight of the coating.

7. The coated article of claim 1 , where the coating comprises 20 to 80% by weight of the hydrophobic compound, and 20 to 80% by weight of the fluorinated surface effect agent, both based on the total solids weight of the coating.

8. The coated article of claim 1 wherein the article is a fiber, textile, fabric, fabric blend, paper, nonwoven, leather, proppant particle, inorganic oxide particle, unglazed concrete, brick, tile, granite, limestone, marble, grout, mortar, statuary, monument, glass, thermoplastic sheet, thermoformed or molded article, foam sheet or article, metal, seed, painted fabric or canvas, or a combination thereof.

9. The coated article of claim 1 , wherein the fluorinated surface effect agent is the fluorinated acrylic copolymer.

10. The coated article of claim 1 , wherein the total solids weight of the coating consists essentially of the weight of the hydrophobic compound and the weight of the at least one fluorinated surface effect agent.

11. The coated article of claim 1 , wherein the article is a fiber, textile, fabric, fabric blend, paper, nonwoven, leather, proppant particle, inorganic oxide particle, unglazed concrete, brick, granite, limestone, marble, grout, mortar, statuary, monument, glass, thermoplastic sheet, foam sheet or article, seed, painted fabric, canvas, or a combination thereof.

12. A coated article comprising a complete permanent fluorinated coating on the surface of an article,
wherein the coating comprises 5 to 99% by weight of a hydrophobic compound, and 1 to 95% by weight of at least one fluorinated surface effect agent, both based on the total solids weight of the coating, wherein the total solids weight of the coating consists of the weight of the hydrophobic compound and the weight of the at least one fluorinated surface effect agent, wherein the hydrophobic compound is selected from a cyclic or acyclic alcohol which is substituted with at least two —R 1 , —C(O)R 1 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 , or mixtures thereof;
where the cyclic or acyclic sugar alcohol is selected from a pentaerythritol, saccharide, reduced sugar, aminosaccharide, citric acid, aldonic acid, or aldonic acid lactone; wherein
each n is independently 0 to 20;
each m is independently 0 to 20;
m+n is greater than 0;
each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons;
each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons;
wherein the fluorinated surface effect agent is a hydrophobic polymer selected from the group consisting of fluorinated cationic acrylic polymers, fluorinated anionic acrylic polymers, fluorinated nonionic acrylic polymers, partially fluorinated urethanes, and mixtures thereof; and
wherein, if the fluorinated surface effect agent is a fluorinated acrylic copolymer, it is a reaction product of monomers comprising:
a) one or more fluorinated ethylenically unsaturated monomers;
b) an ethylenically unsaturated monomer having a polar or reactive group; and
c) one or more monomers selected from a second ethylenically unsaturated monomer having a polar or reactive group, or a non-fluorinated ethylenically unsaturated hydrophobic monomers excluding cyclohexyl acrylate or methyl acrylate wherein the homopolymer of hydrophobic monomer c) has a maximum glass transition temperature (T g ) of 45° C. and/or a maximum melt transition temperature (T m ) of 25° C.

13. The coated article of claim 12 , where the hydrophobic compound is selected from formulas (la), (Ib), or (Ic):

wherein each R is independently —H; —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2

Assignees

• Chemours Co Fc Llc

Inventors

• Brown Gerald Oronde
• Sworen John Christopher
• Crosetto Tess
• Karanja Charles

Classifications

• C08F2/22

  Emulsion polymerisation · CPC title

• C08K5/1535

  Five-membered rings · CPC title

• C09D5/1681 Primary

  Antifouling coatings characterised by surface structure, e.g. for roughness effect giving superhydrophobic coatings or Lotus effect · CPC title

• D06M23/10

  Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof · CPC title

• D06M13/224

  Esters of carboxylic acids; Esters of carbonic acid · CPC title